Mandelic Acid → Carbamazepine

HRID 41349

Reaction equation

HRID 41349 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[O-:16][C:17]#[N:18].[Na+].C(O)(=O)C(C1C=CC=CC=1)O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:17]([NH2:18])=[O:16])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1

Participants

6

Reactant 4

HCID 1292Mandelic AcidHCID 9212Dibenz(b,f)azepineHCID 14798Sodium HydroxideHCID 517096Sodium Cyanate

Product 1

HCID 2554CarbamazepineYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 10 g of iminostilbene in 100 ml toluene was treated with 20.2 g of sodium cyanate and 27.5 g of mandelic acid and was heated to reflux for about 10 hrs. The reaction mixture was cooled to room temperature and charged with sodium hydroxide solution and maintained for 8 hrs. The resulting suspension was filtered, washed with water and dried to give 11 g of carbamazepine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 10 hrs
  3. temperaturemaintained for 8 hrs
  4. filtrationThe resulting suspension was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-9156a4b6f0a14fffb3d533decc5b9669
Source dataset
uspto-grants-2013_09
Patent number
US08530647B2

Linked notes

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